dc.date.accessioned | 2023-03-06T18:26:24Z | |
dc.date.available | 2023-03-06T18:26:24Z | |
dc.date.created | 2022-11-17T14:52:49Z | |
dc.date.issued | 2022 | |
dc.identifier.citation | Andrei, Mioara Undheim, Kjell . Azolo substitution into the purine scaffold in nucleoside cyclic 3',5'-phosphorothioates. Monatshefte für Chemie. 2022, 153(12), 1213-1223 | |
dc.identifier.uri | http://hdl.handle.net/10852/100954 | |
dc.description.abstract | Abstract Azolation in the 8-position in the purine scaffold of cAMP (adenosine 3′,5′-cyclic monophosphate) and cAMPS (adenosine 3′,5′-cyclic monophosphorothioate) provided derivatives with an azole ring directly attached to the purine via an annular azole nitrogen. Electrophilic bromination in the 8-position was followed by nucleophilic substitution with metalated azoles to afford 8-imidazo and 8-triazolo derivatives. The substrates were appropriately protected ( S p )-3′,5′-cyclic N -benzylphosphoramidate. A subsequent carbon disulfide promoted thiation reaction afforded corresponding ( R p )-8-azolo-3′.5′-cAMPS products. The reactions were stereoselective. The products as tri- n- butylammonium salts were soluble in organic solvents and were purified by chromatography. The ammonium salts were converted to sodium salts.
Graphical abstract | |
dc.language | EN | |
dc.rights | Attribution 4.0 International | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.title | Azolo substitution into the purine scaffold in nucleoside cyclic 3',5'-phosphorothioates | |
dc.title.alternative | ENEngelskEnglishAzolo substitution into the purine scaffold in nucleoside cyclic 3',5'-phosphorothioates | |
dc.type | Journal article | |
dc.creator.author | Andrei, Mioara | |
dc.creator.author | Undheim, Kjell | |
cristin.unitcode | 185,15,12,0 | |
cristin.unitname | Kjemisk institutt | |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 1 | |
dc.identifier.cristin | 2075731 | |
dc.identifier.bibliographiccitation | info:ofi/fmt:kev:mtx:ctx&ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Monatshefte für Chemie&rft.volume=153&rft.spage=1213&rft.date=2022 | |
dc.identifier.jtitle | Monatshefte für Chemie | |
dc.identifier.volume | 153 | |
dc.identifier.issue | 12 | |
dc.identifier.startpage | 1213 | |
dc.identifier.endpage | 1223 | |
dc.identifier.doi | https://doi.org/10.1007/s00706-022-02980-2 | |
dc.type.document | Tidsskriftartikkel | |
dc.type.peerreviewed | Peer reviewed | |
dc.source.issn | 0026-9247 | |
dc.type.version | PublishedVersion | |